CN1325492C - Beta-isoindigo coloring agent - Google Patents
Beta-isoindigo coloring agent Download PDFInfo
- Publication number
- CN1325492C CN1325492C CNB2003801021768A CN200380102176A CN1325492C CN 1325492 C CN1325492 C CN 1325492C CN B2003801021768 A CNB2003801021768 A CN B2003801021768A CN 200380102176 A CN200380102176 A CN 200380102176A CN 1325492 C CN1325492 C CN 1325492C
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- alkyl
- compound
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- amino
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/04—Isoindoline dyes
Abstract
The invention relates to a compound of general formula (I) in which C represents an alicyclic or heterocyclic group having C<2v> symmetry, and B represents ortho-C<6>-C<18>-arylene. The invention also relates to a method for producing this compound and to the use thereof as a coloring agent for coloring or pigmenting organic or inorganic high-molecular or low-molecular, particularly high-molecular, organic materials.
Description
The present invention relates to novel pigment dyestuff and dyestuff.
In the tinting material field, always to having high anti-migration fastness and light fastness, good thermostability and high tinctorial strength, and under the situation of pigment, there is the market requirement in the new tone that also has high fastness to solvent.
US2,254,354 have described the β-isoindigo compound that is replaced by cyclic group, described cyclic group contain at least one=CH
2-CO-group.But, mentioned therein compound obfuscation.
The purpose that exists provides improved β-isoindigo pigment, and described β-isoindigo pigment also has purity and the brightness higher than pigment of the prior art except above-mentioned pigment performance.
Found the compound realization of through type (I) astoundingly of described purpose.
Therefore, the invention provides the compound of general formula (I),
Wherein, C is for having C
2vSymmetric alicyclic group or heterocyclic group, and B is adjacent (C
6-C
18) arylidene.
The compound of preferred formula (I) is symmetric, and promptly group B is identical separately and group C is identical separately.
Also preferably wherein B be adjacent phenylene or 2, the compound of the formula of 3-naphthylidene (I).
The compound of preferred formula (I) wherein encircles the C that has that C meets formula (a) to (d) in addition
2vSymmetric member ring systems,
Wherein, R
1And R
2Independently of one another, be hydrogen, C
1-C
25Alkyl, C
5-C
12Cycloalkyl, C
6-C
24Aryl, C
1-C
25Alkyl-(C
6-C
10) aryl, have 1,2 or 3 heteroatomic heteroaromatic group that is selected from N, O and S ,-(CH
2)
n-COR
3Or-(CH
2)
m-OR
4,
Wherein, R
3For hydroxyl, do not replace or with hydroxyl or the amino C that replaces one or many
1-C
25Alkoxyl group, C
1-C
25Alkylamino, two (C
1-C
25Alkyl) amino, C
1-C
25Alkyl-C
6-C
24Arylamino, (C
6-C
24Aryl) amino, two (C
6-C
24Aryl) amino or C
2-C
24Alkene oxygen base,
And R
4For hydrogen or-CO-(C
1-C
25Alkyl), and n and m are independently of one another, are the integer of 0-6, the integer of preferred 1-4, and wherein at R
1, R
2, R
3And R
4In, the C-C unit also can be substituted by ether unit C-O-C, and
X is=O ,=S or=NR
2,
And R
5And R
6Independently of one another, be hydrogen, halogen, CN, R
1, OR
1, SR
1, NR
1R
2, NO
2, SO
2(OR
1), SO
2R
1, SO
2NR
1R
2Or PO
2(OR
1).
C
2vSymmetric notion has description in technical literature.
As C
2vSymmetric molecule, the symmetry element that the substituting group C in the compound of formula (I) has identity, a C
2Axle and two minute surfaces, orthogonal and its intersection of described two minute surfaces obtains C
2Axle.
R
1And R
2Be preferably hydrogen, C especially
1-C
18Alkyl, C
5-C
6Cycloalkyl, C
6-C
10Aryl, benzyl, pyridyl, pyrryl, thienyl, imidazolyl, azoles base, thiazolyl, pyrimidyl, hydroxycarbonyl group-(C
0-C
18) alkyl, C
1-C
18Alkoxy carbonyl-(C
0-C
18) alkyl, aminocarboxyl-(C
0-C
18) alkyl, C
1-C
18Alkyl amino-carbonyl-(C
0-C
18) alkyl, C
6-C
10Aromatic yl aminocarbonyl-(C
0-C
18) alkyl, two (C
1-C
18Alkyl) aminocarboxyl-(C
0-C
18) alkyl, C
1-C
18Alkyl-(C
6-C
10) aromatic yl aminocarbonyl-(C
0-C
18) alkyl and two (C
6-C
10Aryl) aminocarboxyl-(C
0-C
18) alkyl.
R
3Be preferably hydroxyl, C especially
1-C
18Alkoxyl group, C
1-C
18Alkylamino, two (C
1-C
18Alkyl) amino, benzylamino, C
6-C
10Arylamino, two (C
6-C
10Aryl) amino or (C
2-C
18) alkene oxygen base.
R
5And R
6Be preferably hydrogen, Cl, Br, C especially
1-C
18Alkyl, C
5-C
6Cycloalkyl, benzyl, C
6-C
10Aryl, pyridyl, pyrryl, thienyl, imidazolyl, azoles base, thiazolyl, pyrimidyl, C
1-C
18Alkoxyl group, C
6-C
10Aryloxy, C
1-C
18Alkyl sulfenyl, C
6-C
10Artyl sulfo, C
1-C
18Alkylamino, C
6-C
10Arylamino, two (C
1-C
18Alkyl) amino, C
1-C
18Alkyl-(C
6-C
10)-arylamino, two (C
6-C
10Aryl) amino, SO
3H, C
1-C
18Alkoxyl group alkylsulfonyl, C
1-C
18Alkyl sulphonyl and two (C
1-C
18Alkyl) amino-sulfonyl.
Making us interested especially is the compound of formula (2) and (3),
Wherein, R
1, R
5And R
6As above definition.
The present invention provides the method for the compound of a kind of preparation general formula (I) in addition, and it is by making the compound of formula (III)
With the ring compound condensation of the formula (IV) of at least 2 molar equivalents and carry out,
Reaction is 10-250 ℃ in temperature suitably, under preferred 100-200 ℃, preferably at high boiling solvent, as N-Methyl pyrrolidone, propylene glycol, 2-phenoxyethyl alcohol, chlorobenzene, 1,2-dichlorobenzene, 1-chloronaphthalene, N are in the accelerine, and if desired, at organic acid, as under the existence of formic acid, acetate and propionic acid or at mineral acid, as carrying out under the existence of sulfuric acid, hydrochloric acid and phosphoric acid.
The compound of general formula (III) can be by self known method (R.P.Smirnov etc., Izv.Vysshikh, Uchebn.Zavednii, Khim.i Khim.Tekhnol.1963,6,1022-4), by in autoclave in the presence of Sodium Nitrite, make [1,1 '] of formula V join different indolylidene (Biisoindolyliden)-3,3 '-dithione and dense ammonia soln are in 110 ℃ of following prepared in reaction.
According to the present invention, the compound of general formula (I) is used for high molecular or low-molecular-weight organic or inorganic material, particularly high-molecular weight organic materials dyeing or painted.
According to the character of its substituent character or high molecular weight organic materials to be colored, compound of the present invention can be used as the dyestuff that dissolves in polymkeric substance or as pigment.Under latter event, advantageously by in the organic solvent that does not dissolve pigment itself and at high temperature, for example under 60-200 ℃, particularly under 70-150 ℃, the preferably aftertreatment under 75-100 ℃, the product (rough pigment) that will form in synthetic changes into the finely divided form that has further improved pigment performance usually.Aftertreatment is preferably made up with grinding or kneading operation.
It can be that the high molecular weight material of organic or inorganic character and plastics and/or natural materials are painted that tinting material of the present invention extremely is suitable for.These materials can be meant, for example natural resin, siccative oil, rubber or casein.They also can be meant modified natural materials uncle, as chlorinated rubber, oil-modified alkyd resin, viscose glue, derivatived cellulose, as cellulose ester or ether of cellulose be meant the complete synthesis organic polymer (plastics) that can obtain by addition polymerization, polycondensation or poly-addition especially.In plastics class by the addition polymerization preparation, can mention following plastics especially: polyolefine, as polyethylene, polypropylene, polyisobutene, with the polyolefine that replaces, as polystyrene, polyvinyl chloride, polyvinylidene dichloride, polyvinylacetal, polyacrylonitrile, polyacrylic acid, polymethyl acrylic acid, polyacrylic ester and polymethacrylate or polyhutadiene with and multipolymer.In plastics class by poly-addition and polycondensation preparation, can mention following plastics: polyester, polymeric amide, polyimide, polycarbonate, urethane, polyethers, polyacetal, and the condensation product (aminoplastics) of the condensation product of formaldehyde and phenols (phenoplast) and formaldehyde and urea, thiocarbamide and melamine.Described material can also be meant siloxanes or silicone resin.
This high molecular weight material can Individual existence or is existed with form that is plastic material or melt or the mixture that is the form of spinning solution.They can also monomer whose form or with polymerization state, with solubilized form, exist with binding agent or printing-ink as membrane-forming agent or lacquer, as Toenol 1140 varnish, Nitrocellulose, Synolac, melamine resin and formaldehyde resin or acrylic resin.
Therefore, compound of the present invention is suitable for use as in oil base or water-based paint, in various coating, in the dazzle paint, it is painted to be used for spinning, be used for the mass coloration of plastics or painted, in graphics industry with in the printing-ink, in paper, fabric or decorating printing, with in the paper mass coloration, be used to prepare printing ink, water base or non-water-based ink-jet ink, micro-emulsion ink and according to the tinting material of the printing ink of hot melt process operation.
Compound of the present invention also is suitable for use as electrofax tinter and photographic developer, as the tinting material in single component or two-pack powder toner (being also referred to as single component or two-component developing agent), magnetic color tuner, liquid toner, polymerization toner and the extraordinary toning agent.Typical toner adhesive is addition polymerization resin, poly-addition resin and condensation resin, as vinylbenzene, cinnamic acrylic ester, styrene butadiene, acrylate, polyester, phenolic aldehyde-Resins, epoxy, polysulfones, urethane, they are used alone or in combination, and polyethylene and polypropylene, it can also comprise other composition, as charge control agent, wax or flow promotor, but or these additives of following adopted carry out modification.
Compound of the present invention is suitable for use as the tinting material in powder and the powder coating in addition, but the tinting material in the powder coating that is coated with of triboelectricity or moving EFI particularly, above-mentioned powder coating can be used for being coated with the surface of the goods of being made by for example metal, timber, plastics, glass, pottery, concrete, textile materials, paper or rubber.Used typical powder coating resin comprises the Resins, epoxy that uses with conventional solidifying agent, the vibrin that contains carboxyl and hydroxyl, urethane resin and acrylic resin.Can also use resin combination.For example, often Resins, epoxy and the vibrin that contains carboxyl and hydroxyl are used in combination.Typically curing agent component (depending on resin system) is, for example acid anhydrides, imidazoles and Dyhard RU 100 and derivative thereof, blocked isocyanate, two acylcarbamates, resol, melamine resin, triglycidyl isocyanurate, azoles quinoline and dicarboxylic acid.
In addition, compound of the present invention is suitable for use as in the water base or non-water-based ink-jet ink and according to the tinting material in those printing ink of hot melt process operation.
It is 0.5 weight %-15 weight % that jetted ink contains total amount usually, one or more compounds of the present invention of preferred 1.5 weight %-8 weight % (calculating based on dry-matter).
Micro-emulsion ink is based on organic solvent, water and if desired, additional hydrotrophy material (interface vehicle).Micro-emulsion ink contains 0.5 weight %-15 weight % usually, one or more compounds of the present invention of preferred 1.5 weight %-8 weight %, organic solvent and/or the hydrotrophy compound of the water of 5 weight %-99 weight % and 0.5 weight %-94.5 weight %." solvent base " jetted ink preferably contains one or more compounds of the present invention of 0.5 weight %-15 weight %, organic solvent and/or the hydrotrophy compound of 85 weight %-99.5 weight %.The hot melt printing ink majority is based on wax, lipid acid, Fatty Alcohol(C12-C14 and C12-C18) or sulphonamide, and it at room temperature is solid liquefaction when heating, and wherein preferred fusion range is between about 60 ℃ and about 140 ℃.Hot melt ink jet ink for example is made up of the wax of 20 weight %-90 weight % and one or more compounds of the present invention of 1 weight %-10 weight % basically.Also can there be the other polymkeric substance (as " dyestuff solvating agent ") of 0 weight %-20 weight %, the dispersing auxiliary of 0 weight %-5 weight %, the viscosity modifier of 0 weight %-20 weight %, the softening agent of 0 weight %-20 weight %, the viscosity additives of 0 weight %-10 weight %, the transparent stablizer (it suppresses for example wax crystallization) of 0 weight %-10 weight % and the oxidation inhibitor of 0 weight %-2 weight % in addition.
In addition, tinting material of the present invention also is applicable to and is used for add lustre to both colour filter of addition and subtraction, and uses tinting material as e-inks (" e-printing ink ") or " electronic paper " (" e-paper ").
Producing so-called colour filter, in reflectivity and both processes of transparent colour filter, will be in the binding agent (acrylate, acrylic acid or the like ester, polyimide, polyvinyl alcohol, epoxide, polyester, melamine, gelatin, casein) that is fit to be paste form or as the LCD element under every kind of situation of pigment paint of painted photoresist material (as the TFT-LCD=Thin Film Transistor-LCD or, as on (S) TN-LCD=(surpassing) twisted nematic-LCD).Except high thermal stability, the pure property of high pigment also is the precondition of stable paste or painted photoresist material.
In addition, painted colour filter also can apply by ink jet printing method or other print process that is fit to.
In addition, the invention provides tinting material of the present invention and be used for the light data storage, be preferred for using laser with the purposes in the optical layers of the light data storage of record data.Tinting material can regulate by substituent character and quantity in applying medium for using necessary solvability.
In addition, compound of the present invention is suitable for use as the tinting material in the makeup, is used to make seed painted and be used to make mineral oil, lubricating grease and wax painted.
Substituent character on The compounds of this invention is decided, painted being characterized as that is obtained has good fastness to heat, light fastness and weather-proof fastness, chemical-resistant and well apply performance, as anti-crystallization fastness and anti-dispersion fastness, and especially have anti-migration fastness, anti-fastness, anti-fastness and the fastness to solvent of being coated with again of oozing out.Compound as the dyestuff that dissolves in polymkeric substance only has low or limited anti-solvent density naturally.
The present invention provides in addition and comprises high molecular or low-molecular-weight organic or inorganic material, the compound compositions at least a of the present invention of high molecular weight organic materials and painted significant quantity particularly, described significant quantity is generally 0.005 weight %-70 weight %, 0.01 weight %-10 weight % particularly is based on the organic or inorganic material.
Embodiment 1:3 joins different indolylidene 3 '-two (1,3-diethyl-2-sulfo--4,6-dioxo tetrahydropyrimidine-5-subunit)-[1,1 ']
10g [1,1 '] joined different indolylidene-3,1 of 3 '-diimine and 23.1g, 3-diethyl-2-thiobarbituricacid stirred 4 hours down in 155 ℃ in the mixture of the Glacial acetic acid of the NMP of 100ml and 100ml.After being cooled to room temperature, with suspension filtered and adopt the washing with alcohol filtration product, adopt water washing and dry down then at 60 ℃.Produce the metal green powder of 21.3g (88%) following formula: compound like this.
Fusing point:＞300 ℃
H-NMR (D
2SO
4): 8.05 (d, 2H), 7.80 (d, 2H), 7.54 (t, 2H), 7.33 (t, 2H), 3.95 (s, wide, 8H), 0.95 (t, 12H).
Embodiment 2:3 joins different indolylidene 3 '-two (1,3-dimethyl-2,4,6-trioxy-tetrahydropyrimidine-5-subunit)-[1,1 ']
10g [1,1 '] joined different indolylidene-3,1 of 3 '-diimine and 18.1g, the 3-dimethyl barbituric acid stirred 5 hours under refluxing in the mixture of the Glacial acetic acid of the NMP of 160m1 and 40ml.After being cooled to room temperature, with suspension filtered and adopt the washing with alcohol filtration product, adopt water washing and dry down then at 60 ℃.Produce the powder near black of 14.5g (70%) following formula: compound like this.
Fusing point:＞300 ℃
MS(m/e)：539[M+H]
+，561[M+Na]
+。
Embodiment 3:3 joins different indolylidene 3 '-two (1, two (the 2-ethylhexyls)-2,4 of 3-, 6-trioxy-tetrahydropyrimidine-5-subunit)-[1,1 ']
10g [1,1 '] joined different indolylidene-3,1 of 3 '-diimine and 40.9g, two (2-ethylhexyl) barbituric acids of 3-stirred 4 hours down in 155 ℃ in the mixture of the Glacial acetic acid of the NMP of 100ml and 100ml.After being cooled to room temperature, with suspension filtered and adopt the washing with alcohol filtration product, adopt water washing and dry down then at 60 ℃.Produce the purple powder of 28.8g (80%) following formula: compound like this.
Fusion range: 198-206 ℃
MALDI (m/e, negative mode): 930[M-H]
-
H-NMR(CDCl
3)：15.14(s，2H)，9.62(d，2H)，8.43(d，2H)，7.88(t，2H)，7.71(t，2H)，4.04(m，8H)，1.94(m，4H)，1.35(m，32H)，1.14(m，24H)。
Embodiment 4:3 joins different indolylidene 3 '-two (1,3-phenylbenzene-2,4,6-trioxy-tetrahydropyrimidine-5-subunit)-[1,1 ']
19.4g [1,1 '] joined different indolylidene-3,1 of 3 '-diimine and 50.0g, 3-phenylbenzene barbituric acid stirred 6 hours under refluxing in the mixture of the Glacial acetic acid of the NMP of 230ml and 350ml.After being cooled to room temperature, with suspension filtered and adopt the washing with alcohol filtration product, adopt water washing and dry down then at 60 ℃.Produce the purple powder of 48.1g (82%) following formula: compound like this.
Fusing point:＞300 ℃
MS(m/e)：787[M+H]
+，809[M+Na]
+
H-NMR(D
2SO
4)：7.63(d，2H)，7.27(d，2H)，7.14(t，2H)，6.97(t，2H)，6.82(m，12H)，6.65(d，8H)。
Embodiment 5:3 joins different indolylidene 3 '-two (1,3-dioxo indane-2-subunit)-[1,1 ']
10.0g [1,1 '] joined different indolylidene-3,1 of 3 '-diimine and 16.9g, 3-dioxo indane stirred 6 hours under refluxing in the mixture of the Glacial acetic acid of the NMP of 100ml and 100ml.After being cooled to room temperature, with suspension filtered and adopt NMP and the mixture of Glacial acetic acid (1: 1) washing and filtering product, adopt washing with alcohol subsequently, adopt water washing and dry down then at 60 ℃.Produce the black powder of 10.8g (54%) following formula: compound like this.
Fusing point:＞300 ℃
MS(m/e)：519[M+H]
+。
Comparative example 1:3 joins different indolylidene 3 '-two (2,4-dioxo-1,4-dihydro-2 H-quinoline-3-subunit)-[1,1 ']
5.0g [1,1 '] joined different indolylidene-3, the 1H-quinoline-2 of 3 '-diimine and 14.9g, the 4-diketone stirred 6 hours under refluxing in the mixture of the Glacial acetic acid of the NMP of 90ml and 10ml.After being cooled to room temperature, with suspension filtered and adopt the washing with alcohol filtration product, adopt water washing and dry down then at 60 ℃.Produce the powder near black of 6.2g (59%) following formula: compound like this.
Fusing point:＞300 ℃
MALDI(m/e)：547[M-H]
-。
Comparative example 2:3 joins different indolylidene 3 '-two (3-methyl-5-oxo-1-(3-carboxyl phenyl)-1,5-pyrazoline-4-subunit)-[1,1 ']
To join [1,1 '] of 10.0g different indolylidene-3, the 3-methyl isophthalic acid of 3 '-diimine and 25.3g-(3-carboxyl phenyl)-2-pyrazolin-5-one stirred 5 hours under refluxing in the mixture of the Glacial acetic acid of the NMP of 160ml and 40ml.After being cooled to room temperature, with suspension filtered and adopt the washing with alcohol filtration product, adopt water washing and dry down then at 60 ℃.Produce the brown-black powder of 21.7g (85%) following formula: compound like this.
Fusing point:＞300 ℃
MS(m/e)：661[M-H]
-。
Comparative example 3:3 joins different indolylidene 3 '-two (3-methyl-5-oxo-1-(3-sulfamyl phenyl)-1,5-pyrazoline-4-subunit)-[1,1 ']
To join [1,1 '] of 10.0g different indolylidene-3, the 3-methyl isophthalic acid of 3 '-diimine and 29.4g-(3-sulfamyl)-2-pyrazolin-5-one stirred 3 hours under refluxing in the mixture of the Glacial acetic acid of the NMP of 240ml and 60ml.After being cooled to room temperature, with suspension filtered and adopt the washing with alcohol filtration product, adopt water washing and dry down then at 60 ℃.Produce the brown-black powder of 26.7g (95%) following formula: compound like this.
Fusing point:＞300 ℃
MALDI(m/e)：731[M-H]
-。
Application Example
In order to estimate the performance of pigment prepared in accordance with the present invention, from multiple known varnish, select based on the alkyd melamine resin varnish (AM) of the aromatic-containing compound of the melamine resin of medium oil alkyd and butanol etherification and select air-dry alkyd varnish (LA) based on the no aromatic substance of long-oil-length soybean Synolac in paint field.
In order to estimate the performance that dissolves in the dyestuff of polymkeric substance of the present invention, select polystyrene, polycarbonate or polyester transparent as the glass as plastics to be colored.Test block is by injection moulding production.
Application Example 1
Use the pigment that derives from embodiment 1 and obtain highly colored coating in LA varnish, described coating is reddish blue under the opacifying property black and situation of brightening under true qualities.
Application Example 2
Use the pigment that derives from embodiment 2 and obtain highly colored coating in LA varnish, described coating is to be red-violet colour under the opacifying property black and the situation of brightening under true qualities.
Application Example 3
Using the pigment that derives from embodiment 3 in polystyrene obtains in true qualities and brightens being purified and highly colored purple test block under the situation.
Application Example 4
Using the pigment that derives from embodiment 3 in polyethylene terephthalate obtains in true qualities and brightens being pure and highly colored purple test block under the situation.
Application Example 5
Use the pigment that derives from embodiment 4 and obtain pure and highly colored coating in AM varnish, described coating is to be red-violet colour under the mulberry and the situation of brightening under true qualities.
Application Example 6
In polycarbonate, use the pigment that derives from embodiment 4 and obtain in true qualities and brighten being highly colored red-violet colour test block under the situation, under true qualities, have red fluorescence.
Use comparative example 1
Use the pigment that derives from comparative example 1 and obtain coating in AM varnish, described coating is bluish voilet under the opacifying property black and situation of brightening under true qualities, and these coating obviously more shade than the coating of the compound that contains embodiment 1-5.
Use comparative example 2
Use the pigment that derives from comparative example 2 and obtain coating in AM varnish, for being purple under the opacifying property black and situation of brightening, these coating obviously more shade than the coating of the compound that contains embodiment 1-5 described coating under true qualities.
Use comparative example 3
In AM varnish, use the pigment that derives from comparative example 2 and obtain highly colored coating, described coating under true qualities under the opacifying property black and situation of brightening for blue, these coating obviously more shade than the coating of the compound that contains embodiment 1-5.
Claims (14)
1. the compound of a general formula (I),
Wherein C is for having C
2vSymmetric alicyclic group or heterocyclic group, and B is adjacent (C
6-C
18) arylidene, and encircle the member ring systems that C meets formula (a) to (d),
Wherein, R
1And R
2Independently of one another, be hydrogen, C
1-C
25Alkyl, C
5-C
12Cycloalkyl, C
6-C
24Aryl, C
1-C
25Alkyl-(C
6-C
10) aryl, have 1,2 or 3 heteroatomic heteroaromatic group that is selected from N, O and S ,-(CH
2)
n-COR
3,-(CH
2)
m-OR
4, or hydroxycarbonyl group-(C
0-C
18) alkyl, C
1-C
18Alkoxy carbonyl-(C
0-C
18) alkyl, aminocarboxyl-(C
0-C
18) alkyl, C
1-C
18Alkyl amino-carbonyl-(C
0-C
18) alkyl, C
6-C
10Aromatic yl aminocarbonyl-(C
0-C
18) alkyl, two (C
1-C
18Alkyl) aminocarboxyl-(C
0-C
18) alkyl, C
1-C
18Alkyl-(C
6-C
10) aromatic yl aminocarbonyl-(C
0-C
18) alkyl or two (C
6-C
10Aryl) aminocarboxyl-(C
0-C
18) alkyl,
Wherein, R
3For hydroxyl, do not replace or by hydroxyl or amino replacement the-inferior or C repeatedly
1-C
25Alkoxyl group, C
1-C
25Alkylamino, two (C
1-C
25Alkyl) amino, C
1-C
25Alkyl-(C
6-C
24) arylamino, (C
6-C
24Aryl) amino, two (C
6-C
24Aryl) amino or C
2-C
24Alkene oxygen base,
And R
4For hydrogen or-CO-(C
1-C
25Alkyl), and n and m are independently of one another, are the integer of 0-6, and wherein at R
1, R
2, R
3And R
4In, the C-C unit is optionally substituted by ether unit C-O-C, and
X is=O ,=S or=NR
2,
And R
5And R
6Independently of one another, be hydrogen, halogen, CN, R
1, OR
1, SR
1, NR
1R
2, NO
2, SO
2(OR
1), SO
2R
1, SO
2NR
1R
2Or PO
2(OR
1).
2. the compound of claim 1, it is characterized by B is adjacent phenylene or 2, the 3-naphthylidene.
3. the compound of claim 1 is characterized by the integer that n and m are 1-4.
4. each compound among the claim 1-3 is characterized by R
1And R
2Identical or different, and be hydrogen, C
1-C
18Alkyl, benzyl, C
5-C
6Cycloalkyl, C
6-C
10Aryl, pyridyl, pyrryl, thienyl, imidazolyl, azoles base, thiazolyl, pyrimidyl.
5. each compound among the claim 1-3 is characterized by R
5And R
6Identical or different, and be hydrogen, C1, Br, C
1-C
18Alkyl, C
5-C
6Cycloalkyl, C
6-C
10Aryl, benzyl, pyridyl, pyrryl, thienyl, imidazolyl, azoles base, thiazolyl, pyrimidyl, C
1-C
18Alkoxyl group, C
6-C
10Aryloxy, C
1-C
18Alkyl sulfenyl, C
6-C
10Artyl sulfo, C
1-C
18Alkylamino, C
6-C
10Arylamino, two (C
1-C
18Alkyl) amino, C
1-C
18Alkyl-(C
6-C
10) arylamino, two (C
6-C
10) arylamino, SO
3H, C
1-C
18Alkoxyl group alkylsulfonyl, C
1-C
18Alkyl sulphonyl or two (C
1-C
18Alkyl) amino-sulfonyl.
6. the compound of claim 1, it is characterized by this compound is the compound of formula (2) or (3),
And R
1, R
5And R
6As defined in claim 1.
7. the compound of claim 4, it is characterized by this compound is the compound of formula (2) or (3),
And R
1, R
5And R
6As defined in claim 4.
8. the compound of claim 5, it is characterized by this compound is the compound of formula (2) or (3),
And R
1, R
5And R
6As defined in claim 5.
9. a method for preparing each compound among the claim 1-8 is characterized by the compound that makes formula (III)
Ring compound condensation with the formula (IV) of at least 2 molar equivalents
10. each compound is used for high molecular or dyeing of low-molecular-weight organic or inorganic material or painted purposes among the claim 1-8.
11. the purposes of claim 10 is characterized in that described compound is used for high-molecular weight organic materials dyeing or painted.
12. the purposes of claim 10, as in oil base or water-based paint, in varnish, dazzle paint, be used for that spinning is painted, the mass coloration that is used for plastics or painted, at printing-ink, at the paper mass coloration, be used for seed, powder coating, be used to prepare printing ink, water base or non-water-based ink-jet ink, micro-emulsion ink and according to the tinting material of the printing ink of hot melt process operation.
13. the purposes of claim 10 is with acting on electrofax tinter and photographic developer, be used for colour filter, be used for e-inks and the tinting material of the optical layers used in the light data storage.
14. a composition, described composition comprise high molecular or low-molecular-weight organic or inorganic material and be each compound among the claim 1-8 of 0.005 weight %-70 weight % based on the consumption of organic or inorganic material.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10302020.9 | 2003-01-21 | ||
| DE10302020A DE10302020A1 (en) | 2003-01-21 | 2003-01-21 | New beta-isoindigo compounds, useful as pigments or dyes in e.g. toners, lacquers, plastics or inks, are obtained by condensation of a bis-isoindolidene-diimine with an alicyclic or heterocyclic compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1708560A CN1708560A (en) | 2005-12-14 |
| CN1325492C true CN1325492C (en) | 2007-07-11 |
Family
ID=32602786
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2003801021768A Expired - Fee Related CN1325492C (en) | 2003-01-21 | 2003-12-13 | Beta-isoindigo coloring agent |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7285663B2 (en) |
| EP (1) | EP1587877B1 (en) |
| JP (1) | JP2006513295A (en) |
| KR (1) | KR20050093841A (en) |
| CN (1) | CN1325492C (en) |
| AT (1) | ATE329968T1 (en) |
| DE (2) | DE10302020A1 (en) |
| ES (1) | ES2266894T3 (en) |
| WO (1) | WO2004065490A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8816040B2 (en) * | 2011-06-24 | 2014-08-26 | University Of Tsukuba | Polymer dye |
| CN103804271B (en) * | 2012-11-06 | 2016-08-10 | 北京大学 | Isoindigo green grass or young crops compounds containing electron withdraw group and preparation thereof and application |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0101954A1 (en) * | 1982-08-10 | 1984-03-07 | Bayer Ag | Isoindolazines, process for their preparation and their use |
| EP0190692A2 (en) * | 1985-02-05 | 1986-08-13 | BASF Aktiengesellschaft | Bisindoline pigments and their use |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2254354A (en) * | 1938-08-02 | 1941-09-02 | Ici Ltd | Organic compound |
-
2003
- 2003-01-21 DE DE10302020A patent/DE10302020A1/en not_active Withdrawn
- 2003-12-13 DE DE50303885T patent/DE50303885D1/en not_active Expired - Fee Related
- 2003-12-13 US US10/542,529 patent/US7285663B2/en not_active Expired - Fee Related
- 2003-12-13 JP JP2004566777A patent/JP2006513295A/en not_active Withdrawn
- 2003-12-13 CN CNB2003801021768A patent/CN1325492C/en not_active Expired - Fee Related
- 2003-12-13 KR KR1020057013406A patent/KR20050093841A/en not_active Application Discontinuation
- 2003-12-13 ES ES03789269T patent/ES2266894T3/en not_active Expired - Lifetime
- 2003-12-13 AT AT03789269T patent/ATE329968T1/en not_active IP Right Cessation
- 2003-12-13 EP EP03789269A patent/EP1587877B1/en not_active Expired - Lifetime
- 2003-12-13 WO PCT/EP2003/014201 patent/WO2004065490A1/en active IP Right Grant
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0101954A1 (en) * | 1982-08-10 | 1984-03-07 | Bayer Ag | Isoindolazines, process for their preparation and their use |
| EP0190692A2 (en) * | 1985-02-05 | 1986-08-13 | BASF Aktiengesellschaft | Bisindoline pigments and their use |
Also Published As
| Publication number | Publication date |
|---|---|
| DE10302020A1 (en) | 2004-07-29 |
| ATE329968T1 (en) | 2006-07-15 |
| DE50303885D1 (en) | 2006-07-27 |
| US20060041034A1 (en) | 2006-02-23 |
| EP1587877A1 (en) | 2005-10-26 |
| US7285663B2 (en) | 2007-10-23 |
| WO2004065490A1 (en) | 2004-08-05 |
| EP1587877B1 (en) | 2006-06-14 |
| CN1708560A (en) | 2005-12-14 |
| KR20050093841A (en) | 2005-09-23 |
| JP2006513295A (en) | 2006-04-20 |
| ES2266894T3 (en) | 2007-03-01 |
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